Cindy Crawford and Val Kilmer dated in Apparently part of the reason they split was Val didn't approve of the advertising she did for a bar. He later. While Schiffer was also rumored to date Bon Jovi's Richie Sambora, she and the former Dated: Adam Levine () Cindy Crawford. Cynthia Ann Crawford (born February 20, ) is an American model and actress. Her years .. Retrieved ^ Jump up . Retrieved January 3, Children: 2 including Kaia Gerber.